Jack and Nora are joined by performer, writer, and producer Charlie Dinkin to discuss #21 on Vanity Fair’s list of the 42 Best Romantic Comedies of All Time: The 40-Year-Old Virgin. In this episode, Nora is fixated on orthodontia, Charlie has a personal vendetta against Funko Pops, and Jack reveals what the boys are really talking about. Wax your chest, power up your cutting-edge combo VHS/DVD player, and let’s get some f***ing French toast!

Topics include:

• 2000s-2010s romcoms (and why they’re largely missing from this list)
• There’s Something About Mary (1998) and zipper-related trauma
• Songs we had to sing in school 

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Mysteries we still haven’t solved:

• Does that Viagra match trick actually work?

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Content warning: Much like this film, this episode goes to some weird and potentially uncomfortable places - from penis-related body horror to pornography to discussions of homophobia and of misogyny (particularly the fear/ threat of violence against women) hinted at in parts of the film. Please tread carefully if these are sensitive topics!

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Where to find us:

• Instagram, TikTok, Threads, and Letterboxd at @whenrommetcom
• Support the future of the show on Ko-fi
• Follow Jack at @thejackgregsonshow
• Follow Nora at @norassic_park
• Follow Charlie Dinkin at @chazzykat (and watch her ITV sketch comedy pilot, Say! Less!, or her Christmas panel show, I Don’t Do… Christmas with Julian Clary)

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Find links to our Spotify playlist, the Vanity Fair list, and more here.

Join the conversation! Give us your take on the films we cover, which romcoms you think should be on the list, or your best “would do/ wouldn’t do/ have done” stories on socials or at [email protected].

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